(1) Field of the Invention
The present invention relates to an amphipathic compound, a high molecular compound using the same, and a process for producing the same.
Since the amphipathic compound of the present invention has at least one double bond in a molecule and is capable of polymerizing with various ethylenically unsaturated compounds, it is a useful compound as a raw material for a synthetic resin. Further, the amphipathic compound of the present invention is a compound which is classified as a reactive surfactant, and a high molecular compound obtained by copolymerizing the amphipathic compound of the present invention with an ethylenically unsaturated compound is used for plasticizers, heat resistant resins, lubricants, antistatic agents, paints, adhesives, dispersants, and additives for cement. A copolymer of the amphipathic compound of the present invention with a hydrophilic ethylenically unsaturated compound is soluble or dispersible in water and useful as a high molecular type surfactant. In particular, the copolymer with (meth)acrylamide has a high utility value as a novel paper making additive, which can improve sizing performance and paper reinforcing performance at the same time.
(2) Description of the Related Art
Japanese Patent Laid-open SHO 63-235595 and HEI 5-125681 disclose alkenyl succinic acid semi-ester and a reaction product of alkyl or alkenyl succinic acid with an alkylene oxide adduct of polyhydric alcohol. However, the amphipathic compound of the present invention is a novel compound which has not so far been reported. Further, the copolymer of the amphipathic compound of the present invention with an ethylenically unsaturated compound is also a novel compound which has not so far been reported.
An object of the present invention is to provide (1) a novel amphipathic compound having a succinic acid derivative skeleton with a polymerizable unsaturated bond, (2) a novel amphipathic compound having phthalic acid and its derivative skeletons, (3) a high molecular compound obtained by copolymerizing the amphipathic compound having a succinic acid derivative skeleton with a copolymerizable ethylenically unsaturated compound, (4) a high molecular compound obtained by copolymerizing the amphipathic compound having phthalic acid and its derivative skeletons with a copolymerizable ethylenically unsaturated compound, (5) a water soluble or dispersible high molecular compound obtained by copolymerizing the amphipathic compound having a succinic acid derivative skeleton with a hydrophilic ethylenically unsaturated compound, (6) a water soluble or dispersible high molecular compound obtained by copolymerizing the amphipathic compound having phthalic acid and its derivative skeletons with the copolymerizable, hydrophilic ethylenically unsaturated compound, and a paper making additive containing the water soluble or dispersible high molecular compounds of (5) and (6) as an active ingredient. Among them, particularly the copolymer with (meth)acrylamide is abbreviated as a PAM group sizing agent.
Further, an another object of the present invention is to provide (7) an emulsion having an ability to form a polymer film having excellent heat resistance and water resistance, in which the amphipathic compound of the present invention is used as an emulsifier, (8) a process for producing an amphipathic high molecular compound having a high molecular weight and a low viscosity by copolymerizing the amphipathic compound of the present invention with a hydrophilic ethylenically unsaturated compound in the presence of a colloidizing agent, and (9) a process for producing an emulsion having a heteromorphic structure, obtained by polymerizing a hydrophobic ethylenically unsaturated compound in the presence of the amphipathic compound of the present invention.
That is, the present invention relates to:
1) an amphipathic compound having a succinic acid skeleton represented by any of the following Formulas (1) to (4): 
wherein R1 is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R2 and R3 are independently a hydrogen atom or a methyl group; R4 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; M is a hydrogen atom, an alkali metal, or an ammonium group; and X is NH or Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2);
2) an amphipathic compound having a succinic acid skeleton represented by any of the following Formulas (5) to (8): 
wherein R1 is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R2 and R3 are independently a hydrogen atom or a methyl group; R4 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O; and m is an integer of 1 to 100;
3) an amphipathic compound in which R1 in Formulas (1) to (4) of 1) is represented by any of the following Formulas (9) to (13): 
wherein R5 and R6 are independently a hydrogen atom, or a linear alkyl group or alkenyl group of C1 to C23, provided that a carbon number of (R5+R6) falls in a range of 3 to 45; 
wherein n is an integer of 0 to 6; 
wherein p is an integer of 0 to 6;
4) an amphipathic compound in which R1 in Formulas (5) to (8) of 2) is represented by any of the following Formulas (9) to (13): 
wherein R5 and R6 are independently a hydrogen atom, or a linear alkyl group or alkenyl group of C1 to C23, provided that a carbon number of (R5+R6) falls in a range of 3 to 45; 
wherein n is an integer of 0 to 6; 
wherein p is an integer of 0 to 6;
5) an amphipathic compound having any of phthalic acid or tetrahydrophthalic acid, hexahydrophthalic acid, norbornenedicarboxylic acid, and norbornanedicarboxylic acid structures represented by following Formulas (14) to (17): 
wherein R7 and R8 are independently a hydrogen atom or a methyl group; R9 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; R10 and R11 are independently a hydrogen atom or a methyl group; M is a hydrogen atom, an alkali metal, or an ammonium group; and X is NH or Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2);
6) a high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of an amphipathic compound having a succinic acid skeleton represented by any of Formulas (18) to (21) or a mixture thereof with 10.0 to 99.9 weight % of a copolymerizable ethylenically unsaturated compound: 
wherein R1 is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R2 and R3 are independently a hydrogen atom or a methyl group; R4 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; M is a hydrogen atom, an alkali metal, or an ammonium group; and Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O;
7) a water soluble or dispersible amphipathic high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (18) to (21) as described in 6) or a mixture thereof with 10.0 to 99.9 weight % of a hydrophilic ethylenically unsaturated compound;
8) a paper making additive containing the water soluble or dispersible amphipathic high molecular compound as described in 7) as an active ingredient;
9) a high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (5) to (8) as described in 2) or a mixture thereof with 10.0 to 99.9 weight % of a copolymerizable ethylenically unsaturated compound;
10) a water soluble or dispersible amphipathic high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by any of Formulas (5) to (8) as described in 2) or a mixture thereof with 10.0 to 99.9 weight % of a hydrophilic ethylenically unsaturated compound;
11) a paper making additive containing the water soluble or dispersible amphipathic high molecular compound as described in 10) as an active ingredient;
12) a high molecular compound having phthalic acid or tetrahydrophthalic acid, hexahydrophthalic acid, norbornenedicarboxylic acid, and norbornanedicarboxylic acid structures on side chains which is obtained by copolymerizing 0.1 to 90.0 weight % of a compound represented by any of Formulas (22) to (25) or a mixture thereof with 10.0 to 99.9 weight % of a copolymerizable ethylenically unsaturated compound: 
wherein R7 and R8 are independently a hydrogen atom or a methyl group; R9 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; R10 and R11 are independently a hydrogen atom or a methyl group; M is a hydrogen atom, an alkali metal, or an ammonium group; and Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O;
13) a water soluble or dispersible amphipathic high molecular compound obtained by copolymerizing 0.1 to 90.0 weight % of the compound represented by Formulas (22) to (25) as described in 12) or a mixture thereof with 10.0 to 99.9 weight % of a hydrophilic ethylenically unsaturated compound;
14) a paper making additive containing the water soluble or dispersible amphipathic high molecular compound as described in 13) as an active ingredient;
15) a reactive surfactant represented by any of Formulas (5) to (8), any of Formulas (18) to (21), or any of Formulas (22) to (25): 
wherein R1 is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R2 and R3 are independently a hydrogen atom or a methyl group; R4 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O; and m is an integer of 1 to 100; 
wherein R1 is a linear or branched saturated hydrocarbon group having 6 to 48 carbon atoms, or a linear or branched unsaturated hydrocarbon group containing 1 to 12 unsaturated double bonds and having 6 to 48 carbon atoms; R2 and R3 are independently a hydrogen atom or a methyl group; R4 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; M is a hydrogen atom, an alkali metal, or an ammonium group; and Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O; 
wherein R7 and R8 are independently a hydrogen atom or a methyl group; R9 is a linear or branched saturated hydrocarbon group having 2 to 6 carbon atoms; R10 and R11 are independently a hydrogen atom or a methyl group; M is a hydrogen atom, an alkali metal, or an ammonium group; and Y is NH, Nxe2x80x94(CH2xe2x80x94CHxe2x95x90CH2), or O;
16) a water-dispersing type resin composition obtained by emulsion-polymerizing 0.1 to 20 weight % of the reactive surfactant as described in 15) with 80 to 99.9 weight % of an ethylenically unsaturated compound;
17) a high molecular surfactant obtained by copolymerizing 0.1 to 50 weight % of the reactive surfactant as described in 15) with 50 to 99.9 weight % of a hydrophilic ethylenically unsaturated compound;
18) a water-dispersing type resin composition obtained by emulsion-polymerizing an ethylenically unsaturated compound in the presence of the high molecular surfactant as described in 17);
19) a process for producing an amphipathic high molecular compound, characterized in that the reactive surfactant as described in 15) is copolymerized with a hydrophilic, nonionic unsaturated compound in an aqueous medium in the presence of a colloidizing agent;
20) a process for producing an amphipathic high molecular compound as described in 19), wherein the reactive surfactant of 0.1 to 90 weight % as described in 15) is copolymerized with the hydrophilic, nonionic ethylenically unsaturated compound of 10 to 99.9 weight % in the aqueous medium in the presence of the colloidizing agent of 0.1 to 10 moles per mole of the reactive surfactant;
21) a process for producing an amphipathic high molecular compound as described in 19) or 20), wherein the colloidizing agent comprises a combination of at least one selected from inorganic acid, organic acid, inorganic base, and organic base;
22) a process for producing an amphipathic high molecular compound as described in 19), wherein the reactive surfactant has at least one carboxyl group in the molecule;
23) a process for producing an amphipathic high molecular compound as described in 22), wherein the 10 to 99.9 weight % of hydrophilic, nonionic ethylenically unsaturated compound is copolymerized with 0.1 to 90 weight % of the reactive surfactant having at least one carboxyl group in the molecule in the aqueous medium in the presence of the colloidizing agent of 0.1 to 10 moles per mole of the reactive surfactant;
24) a process for producing an amphipathic high molecular compound as described in 23), wherein the colloidizing agent comprises a combination of at least one selected from inorganic acid, organic acid, inorganic base, and organic base; and
25) a water dispersible type resin composition obtained by emulsion-polymerizing an ethylenically unsaturated compound in the presence of the amphipathic high molecular compound as described in 17).